D-galactose, 2,3,4,5,6-pentaacetate → 1-deoxy-1-(4-hydroxyphenylthio)-2,3,4,6-tetra-O-acetyl-beta-D-galactopyranose

HRID 1637438

Reaktionsgleichung

Reaktionsgleichung von HRID 1637438
[C:1]([O:4][C@H:5]([C@H:8]([C@H:13]([C@@H:18]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:19][C:20](=[O:22])[CH3:21])[O:14][C:15](=[O:17])[CH3:16])[O:9][C:10](=O)C)C=O)(=[O:3])[CH3:2].[OH:28][C:29]1[CH:34]=[CH:33][C:32]([SH:35])=[CH:31][CH:30]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:28][C:29]1[CH:34]=[CH:33][C:32]([S:35][C@@H:10]2[O:9][C@H:8]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[C@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:23]2[O:24][C:25](=[O:27])[CH3:26])=[CH:31][CH:30]=1

Komponenten

5

Edukt 3

HCID 81232D-galactose, 2,3,4,5,6-pentaacetateHCID 2401474-MercaptophenolHCID 516892Sodium Bicarbonate

Produkt 1

HCID 702546491-deoxy-1-(4-hydroxyphenylthio)-2,3,4,6-tetra-O-acetyl-beta-D-galactopyranoseAusbeute 100,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of galactose pentaacetate (3.30 g, 8.50 mmol) and 4-hydroxy-thiophenol (1.40 g, 11.1 mmol) in 50 mL of methylene chloride at -78° C. is added boron trifluoride diethyl ether complex (2.10 mL, 17.1 mmol ). The solution is allowed to warm slowly to 0° C. and then stirred for an additional hour at 0° C. The mixture is poured into saturated aqueous NaHCO3 (200 mL) and extracted with CH2Cl2 (2×150 mL), dried over Na2SO4, concentrated, and purified by flash chromatography (50% EtOAc/hexane) to give 3.90 g (99%) of 1-deoxy-1-(4-hydroxyphenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 78 as a white solid: Rf 0.3 (50% EtOAc/hexane); 1H NMR (CDCl3, 300 MHz) δ 7.42 (d, J=8.6 Hz, 2H), 6.79 (d, J=8.6 Hz, 2H), 5.78 (br s, 1H), 5.39 (d, J=2.56 Hz, 1H, H-4), 5.15 (t, J=9.9 Hz, 1H, H-2), 5.00 (dd, J=3.3, 9.9 Hz, 1H, H-3), 4.56 (d, J=9.9 Hz, 1H, H-1), 4.19 (dd, J=6.6, 11.0 Hz, 1H), 4.09 (dd, J=6.6, 11.0 Hz, 1H), 3.89 (t, J=6.6 Hz, 1H, H-5), 2.12 (s, 3H, OAc), 2.09 (s, 3H, OAc), 2.05 (s, 3H, OAc), 1.97 (s, 3H, OAc).

Aufarbeitung

  1. extractionextracted with CH2Cl2 (2×150 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by flash chromatography (50% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-71800a2ec1be47688ff1901b8ebc20b2
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06040433

Verknüpfte Notizen

Wird geladen…